The copper-catalyzed reaction of aromatic halides with amines or ammonium hydroxide is known.
Sato et al., Synthesis, (1981), pages 472-473, have recited reaction between iodobenzene and phthalimide, in the presence of copper (I) oxide in refluxing collidine.
Groggins, "Unit Processes in Organic Synthesis," McGraw-Hill (5th ed, 1958), has analyzed the ammonolysis of chlorobenzene by ammonium hydroxide in the presence of cuprous oxide. As shown in FIGS. 8-18, on page 458, amination of chlorobenzene is very slow at 160.degree. C. Satisfactory rates for conversion of chlorobenzene to aniline are observed at 200.degree.-210.degree. C.
Nishiyama et al., in U.S. Pat. No. 4,380,670, have proposed converting 3,5-diaminochlorobenzene to 1,3,5-triaminobenzene with aqueous ammonium hydroxide, in the presence of cuprous chloride catalyst, preferably at 160.degree.-190.degree. C.
Conversion of 4-bromo-o-xylene to 3,4-dimethylaniline has been accomplished by reaction with ammonium hydroxide in the presence of cuprous chloride and copper at 195.degree. C. This conversion is reported in Organic Syntheses, Coll. Vol 3, John Wiley, New York (1955), pages 307-309.
Cheveney et al, in U.S. Pat. No. 3,865,876, have recited converting 3,3'-dichlorobenzidine to 3,3'-diaminobenzidine using cuprous chloride catalyst and reaction temperature of 225.degree. C. or higher.
Hale et al. in U.S. Pat. No. Re. 17,280, have proposed converting aromatic halides, e.g. chlorobenzene, to amines using aqueous ammonia solution in the presence of cuprous chloride at 150.degree.-250.degree. C.
Tan et al., in U.S. Pat. No. 4,711,964, disclose preparation of phthalimidobenzocyclobutene derivatives from an aminobenzocyclobutene.
It is an object of this invention to provide low temperature processes for the preparation of aminobenzocyclobutene compounds so as to prevent premature oligomerization or polymerization of resulting aminobenzocyclobutene products.